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yield. The salt may be separated and purified at this stage or alternatively the crude reaction mixture can be treated with sodium carbonate and the free amine extracted with solvent. Results obtained wfith several benzaldehydes are shown in Table I. Our Table I Amines from Reductive Amixation of Benzaldehydes Aldehyde0 Amine product % yield6. c, Bp, °C (mm) Benzaldehyde Benzylamine 59 182-184 (atm)d p-Methoxy benzaldehyde p-Methoxy benzylamine 64 121-123 (14)e o-Chlorobenzaldehyde o-Chlorobenzylamine 70 99.5-102 (11)/ p-Chlorobenzaldehyde p-Ghlorob.nzy lamine 77 106-108 vll-12)0 " Liquid aldehydes were freshly distilled before use; p-chloro-

A series of cyproheptadine derivatives having furan nuclei fused to the 10,11-vinylene bridge has been prepared. None of the compounds retain the potent antiserotonin and antihistaminic actions of cyproheptadine. 1-methyl-4-(1-methyl-8H-dibenzo[a,e]furo[3,4-c]cyclohepten-8-ylidene)piperidine (7), 1-methyl-4-(1,3-dihydro-1-oxo-8H-[3,4:6,7]cycloheptal[1,2-c]furan-8-ylidene)piperidine (10), and its reduction product 11 retained the peripheral anticholinergic activity of cyproheptadine.

A series of trichloroacetamidine derivatives, obtained by addition of amines to trichloroacetonitrile, was evaluated for positive inotropic activity on isolated cat heart papillary muscles. Increased contractility, not antagonized by beta-adrenergic blockade with sotalol or reserpine pretreatment, was observed in this assay with a variety of N-substituted trichloroacetamidine derivatives. More extensive pharmacological studies with the 3-indolylmethyl analogue 2 showed that this amidine in dogs, 5 mg/kg iv, produced a positive inotropic effect more pronounced than that of ouabain, 50 microgram/kg iv. Several of the trichloroacetamidines were found to be inhibitors of guinea pig kidney and calf heart Na-K-dependent ATPase and to have specificity for these enzymes different from that of ouabain. Bacterial mutagenic activity was observed with three members, 2,3, and 12, of the series.

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